ArticleACS catalysis2022
Nickel-Catalyzed Defluorinative Coupling of Aliphatic Aldehydes with Trifluoromethyl Alkenes.
Article in ACS catalysis, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Nickel-Catalyzed Enantioselective Coupling Reactions of Fluorinated Sorbamides with Aldehydes AffordingJournal of the American Chemical Society · 2026Article
- Catalytic 1,2-Migratory Insertion in a Bismuth Redox Platform: Reductive Arylation of Aldehydes.Angewandte Chemie (International ed. in English) · 2025Article
- Redox-neutral photocatalytic cleavage andScience advances · 2025Article
- Ligand-Metal Cooperation Enables Net Ring-Opening C-C Activation / Difunctionalization of Cyclopropyl Ketones.ACS catalysis · 2023Article
- Stereospecific Nickel-Catalyzed Cross-Electrophile Coupling Reaction of Alkyl Mesylates and Allylic Difluorides to Access Enantioenriched Vinyl Fluoride-Substituted Cyclopropanes.ACS catalysis · 2023Article
- Catalytic defluorinative ketyl-olefin coupling by halogen-atom transfer.Chemical science · 2022Article
- Ni-Catalyzed Enantioselective Dialkyl Carbinol Synthesis via Decarboxylative Cross-Coupling: Development, Scope, and Applications.Journal of the American Chemical Society · 2022Article
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2 authors.
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Abstract
A simple procedure is reported for the nickel-catalyzed defluorinative alkylation of unactivated aliphatic aldehydes. The process involves the catalytic reductive union of trifluoromethyl alkenes with aldehydes using a nickel complex of a 6,6'-disubstituted bipyridine ligand with zinc metal as the terminal reductant. The protocol is distinguished by its broad substrate scope, mild conditions, and simple catalytic setup. Reaction outcomes are consistent with the intermediacy of an α-silyloxy(alkyl)nickel intermediate generated by a low-valent nickel catalyst, silyl electrophile, and the aldehyde substrate. Mechanistic findings with cyclopropanecarboxaldehyde provide insights into nature of the reactive intermediates and illustrate fundamental reactivity differences that are governed by subtle changes in ligand and substrate structure.
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